2-(2-Chloro-4-nitro-phenylsulfanyl)-benzothiazole-6-carbonitrile → 2-(4-Amino-2-chloro-phenylsulfanyl)-benzothiazole-6-carbonitrile

HRID 1865537Notes

Reaction equation

HRID 1865537 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[S:11][C:12]1[S:13][C:14]2[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:15]=2[N:16]=1.O.O.[Sn](Cl)(Cl)(Cl)Cl>>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([S:11][C:12]2[S:13][C:14]3[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:15]=3[N:16]=2)=[C:2]([Cl:1])[CH:7]=1

Participants

3

Reactant 2

HCID 221488292-(2-Chloro-4-nitro-phenylsulfanyl)-benzothiazole-6-carbonitrileHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 221487782-(4-Amino-2-chloro-phenylsulfanyl)-benzothiazole-6-carbonitrileYield 93%

Procedure

The title compound was prepared using the method of example 270, starting with 2-(2-chloro-4-nitro-phenylsulfanyl)-benzothiazole-6-carbonitrile (261) (1.6 g, 4.6 mmol), tin chloride dihydrate (Aldrich, 5.21 g, 23.1 mmol). Compound 273 (1.36 g, 93%) was obtained as a yellowish solid. MS (M+H) 318.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-b75c0746b5634329941a5b7bd3718b20
Source dataset
uspto-grants-2009_12
Patent number
US07626033B2

Reaction notes

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